Chemoselective methionine 18F-fluorination on unprotected peptides for positron-emission tomography imaging

2020 Fiscal Year Annual Research Report

• Project/Area Number: 19K17156
• Research Institution: National Institutes for Quantum and Radiological Science and Technology
• Principal Investigator: 胡 寛 国立研究開発法人量子科学技術研究開発機構, 放射線医学総合研究所 先進核医学基盤研究部, 博士研究員(任常) (00827678)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: methionine / 18F-fluorination / peptide / chemoselective / PET / ReACT / oxaziridine / radiotracer

Outline of Annual Research Achievements

I developed a strategy for chemoselective 18F-methionine bioconjugation through a redox activated chemical tagging (ReACT). To achieve this,I started from synthesis of Met-containing dipeptides. Then I investigated the labeling condition, substrate scope, selectivity and applicability of this method. Moreover, to study the clinical utility of this method, I labeled a CD133 binding peptide using this method. The 18F labeling did not alter the original binding ability to CD133. I next performed PET/CT imaging with this tracer in B16F10-bearing C57BL/6J mice.

Research Products

• [Journal Article] Flexible Supercapacitors Based on Graphene/Boron Nitride Nanosheets Electrodes and PVA/PEI Gel Electrolytes (2021)
  • Author(s): Wang Chan、Hu Kuan、Liu Ying、Zhang Ming-Rong、Wang Zhiwei、Li Zhou
  • Journal Title: Materials Volume: 14 Pages: 1955～1955
  • DOI: 10.3390/ma14081955
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Recent developments on PET radiotracers for TSPO and their applications in neuroimaging (2021)
  • Author(s): Zhang Lingling、Hu Kuan、Shao Tuo、Hou Lu、Zhang Shaojuan、Ye Weijian、Josephson Lee、Meyer Jeffrey H.、Zhang Ming-Rong、Vasdev Neil、Wang Jinghao、Xu Hao、Wang Lu、Liang Steven H.
  • Journal Title: Acta Pharmaceutica Sinica B Volume: 11 Pages: 373～393
  • DOI: 10.1016/j.apsb.2020.08.006
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Development of a highly-specific 18F-labeled irreversible positron emission tomography tracer for monoacylglycerol lipase mapping (2021)
  • Author(s): Chen Zhen、Mori Wakana、Rong Jian、Schafroth Michael A.、Shao Tuo、Van Richard S.、Ogasawara Daisuke、Yamasaki Tomoteru、Hiraishi Atsuto、Hatori Akiko、Chen Jiahui、Zhang Yiding、Hu Kuan、Fujinaga Masayuki、Sun Jiyun、Yu Qingzhen、Collier Thomas L.、et al.
  • Journal Title: Acta Pharmaceutica Sinica B Volume: In press Pages: In press
  • DOI: 10.1016/j.apsb.2021.01.021
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] PET Imaging of VEGFR with a Novel 64Cu-Labeled Peptide (2020)
  • Author(s): Hu Kuan、Shang Jingjie、Xie Lin、Hanyu Masayuki、Zhang Yiding、Yang Zhimin、Xu Hao、Wang Lu、Zhang Ming-Rong
  • Journal Title: ACS Omega Volume: 5 Pages: 8508～8514
  • DOI: 10.1021/acsomega.9b03953
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Harnessing the PD-L1 interface peptide for positron emission tomography imaging of the PD-1 immune checkpoint (2020)
  • Author(s): Hu Kuan、Xie Lin、Hanyu Masayuki、Zhang Yiding、Li Lingyun、Ma Xiaohui、Nagatsu Kotaro、Suzuki Hisashi、Wang Weizhi、Zhang Ming-Rong
  • Journal Title: RSC Chemical Biology Volume: 1 Pages: 214～224
  • DOI: 10.1039/D0CB00070A
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Marriage of black phosphorus and Cu2+ as effective photothermal agents for PET-guided combination cancer therapy (2020)
  • Author(s): Hu Kuan、Xie Lin、Zhang Yiding、Hanyu Masayuki、Yang Zhimin、Nagatsu Kotaro、Suzuki Hisashi、Ouyang Jiang、Ji Xiaoyuan、Wei Junjie、Xu Hao、Farokhzad Omid C.、Liang Steven H.、Wang Lu、Tao Wei、Zhang Ming-Rong
  • Journal Title: Nature Communications Volume: 11 Pages: 2778
  • DOI: 10.1038/s41467-020-16513-0
  • Open Access / Int'l Joint Research
• [Journal Article] Self-Assembly of Constrained Cyclic Peptides Controlled by Ring Size (2020)
  • Author(s): Hu Kuan、Xiong Wei、Sun Chengjie、Wang Chan、Li Jingxu、Yin Feng、Jiang Yixiang、Zhang Ming-Rong、Li Zhou、Wang Xinwei、Li Zigang
  • Journal Title: CCS Chemistry Volume: 2 Pages: 42～51
  • DOI: 10.31635/ccschem.020.201900047
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Boron agents for neutron capture therapy (2020)
  • Author(s): Hu Kuan、Yang Zhimin、Zhang Lingling、Xie Lin、Wang Lu、Xu Hao、Josephson Lee、Liang Steven H.、Zhang Ming-Rong
  • Journal Title: Coordination Chemistry Reviews Volume: 405 Pages: 213139～213139
  • DOI: 10.1016/j.ccr.2019.213139
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Customization of Conductive Elastomer Based on PVA/PEI for Stretchable Sensors (2020)
  • Author(s): Wang Chan、Hu Kuan、Zhao Chaochao、Zou Yang、Liu Ying、Qu Xuecheng、Jiang Dongjie、Li Zhe、Zhang Ming‐Rong、Li Zhou
  • Journal Title: Small Volume: 16 Pages: 1904758～1904758
  • DOI: 10.1002/smll.201904758
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Smart Titanium Coating Composed of Antibiotic Conjugated Peptides as an Infection‐Responsive Antibacterial Agent (2020)
  • Author(s): Zhang Yunfei、Hu Kuan、Xing Xuan、Zhang Jingshuang、Zhang Ming‐Rong、Ma Xiaohui、Shi Rui、Zhang Liqun
  • Journal Title: Macromolecular Bioscience Volume: 21 Pages: 2000194～2000194
  • DOI: 10.1002/mabi.202000194
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and preliminary evaluation of 4-hydroxy-6-(3-[11C]methoxyphenethyl)pyridazin-3(2H)-one, a 11C-labeled -amino acid oxidase (DAAO) inhibitor for PET imaging (2020)
  • Author(s): Deng Xiaoyun、Zhang Yiding、Chen Zhen、Kumata Katsushi、Van Richard、Rong Jian、Shao Tuo、Hatori Akiko、Mori Wakana、Yu Qingzhen、Hu Kuan、Fujinaga Masayuki、Wey Hsiao-Ying、Shao Yihan、Josephson Lee、Murtas Giulia、Pollegioni Loredano、Zhang Ming-Rong、Liang Steven
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 30 Pages: 127326～127326
  • DOI: 10.1016/j.bmcl.2020.127326
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and preliminary evaluation of 18F-labeled 1-(6,7-dimethyl-4-(methylamino)-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)-2-(trans-2-(6-fluoropyridin-3-yl)cyclopropyl)ethan-1-one for imaging muscarinic acetylcholine receptor subtype 4 (2020)
  • Author(s): Deng Xiaoyun、Zhang Yiding、Rong Jian、Kumata Katsushi、Shao Tuo、Wang Gangqiang、Hatori Akiko、Mori Wakana、Yu Qingzhen、Hu Kuan、Fujinaga Masayuki、Shao Yihan、Josephson Lee、Sun Shaofa、Zhang Ming-Rong、Liang Steven
  • Journal Title: Tetrahedron Letters Volume: 61 Pages: 152060～152060
  • DOI: 10.1016/j.tetlet.2020.152060
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Radiotheranostic Agent 64Cu-cyclam-RAFT-c(-RGDfK-)4 for Management of Peritoneal Metastasis in Ovarian Cancer (2020)
  • Author(s): Jin Zhao-Hui、Tsuji Atsushi B.、Degardin Melissa、Sugyo Aya、Obara Satoshi、Wakizaka Hidekatsu、Nagatsu Kotaro、Hu Kuan、Zhang Ming-Rong、Dumy Pascal、Boturyn Didier、Higashi Tatsuya
  • Journal Title: Clinical Cancer Research Volume: 26 Pages: 6230～6241
  • DOI: 10.1158/1078-0432.CCR-20-1205
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] 3-(Cyclopropylmethyl)-7-((4-(4-[11C]methoxyphenyl)piperidin-1-yl)methyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine: Synthesis and preliminary evaluation for PET imaging of metabotropic glutamate receptor subtype 2 (2020)
  • Author(s): Kumata Katsushi、Zhang Yiding、Ogawa Masanao、Kurihara Yusuke、Mori Wakana、Hu Kuan、Fujinaga Masayuki、Nengaki Nobuki、Zhang Ming-Rong
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 30 Pages: 127555～127555
  • DOI: 10.1016/j.bmcl.2020.127555
  • Peer Reviewed
• [Journal Article] A Hybrid Biofuel and Triboelectric Nanogenerator for Bioenergy Harvesting (2020)
  • Author(s): Li Hu、Zhang Xiao、Zhao Luming、Jiang Dongjie、Xu Lingling、Liu Zhuo、Wu Yuxiang、Hu Kuan、Zhang Ming-Rong、Wang Jiangxue、Fan Yubo、Li Zhou
  • Journal Title: Nano-Micro Letters Volume: 12 Pages: 50
  • DOI: 10.1007/s40820-020-0376-8
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Identification and Development of a New Positron Emission Tomography Ligand 4-(2-Fluoro-4-[11C]methoxyphenyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)picolinamide for Imaging Metabotropic Glutamate Receptor Subtype 2 (mGlu2) (2020)
  • Author(s): Yamasaki Tomoteru、Zhang Xiaofei、Kumata Katsushi、Zhang Yiding、Deng Xiaoyun、Fujinaga Masayuki、Chen Zhen、Mori Wakana、Hu Kuan、Wakizaka Hidekatsu、Hatori Akiko、Xie Lin、Ogawa Masanao、Nengaki Nobuki、Van Richard、Shao Yihan、Sheffler Douglas J.、Cosford Nicholas D. P.、Liang Steven H.、Zhang Ming-Rong
  • Journal Title: Journal of Medicinal Chemistry Volume: 63 Pages: 11469～11483
  • DOI: 10.1021/acs.jmedchem.9b01991
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and evaluation of 6-(11C-methyl(4-(pyridin-2-yl)thiazol-2-yl)amino)benzo[d]thiazol-2(3H)-one for imaging γ-8 dependent transmembrane AMPA receptor regulatory protein by PET (2020)
  • Author(s): Yu Qingzhen、Kumata Katsushi、Li Hua、Zhang Yiding、Chen Zhen、Zhang Xiaofei、Shao Tuo、Hatori Akiko、Yamasaki Tomoteru、Xie Lin、Hu Kuan、Wang Gangqiang、Josephson Lee、Sun Shaofa、Zhang Ming-Rong、Liang Steven H.
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 30 Pages: 126879～126879
  • DOI: 10.1016/j.bmcl.2019.126879
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and preliminary studies of 11C-labeled tetrahydro-1,7-naphthyridine-2-carboxamides for PET imaging of metabotropic glutamate receptor 2 (2020)
  • Author(s): Zhang Xiaofei、Zhang Yiding、Chen Zhen、Shao Tuo、Van Richard、Kumata Katsushi、Deng Xiaoyun、Fu Hualong、Yamasaki Tomoteru、Rong Jian、Hu Kuan、Hatori Akiko、Xie Lin、Yu Qingzhen、Ye Weijian、Xu Hao、Sheffler Douglas J.、Cosford Nicholas D. P.、Shao Yihan、Tang Pingping、Wang Lu、Zhang Ming-Rong、Liang Steven H.
  • Journal Title: Theranostics Volume: 10 Pages: 11178～11196
  • DOI: 10.7150/thno.42587
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Synthesis and preliminary evaluation of novel 11C-labeled GluN2B-selective NMDA receptor negative allosteric modulators (2020)
  • Author(s): Sun Ji-yun、Kumata Katsushi、Chen Zhen、Zhang Yi-ding、Chen Jia-hui、Hatori Akiko、Fu Hua-long、Rong Jian、Deng Xiao-yun、Yamasaki Tomoteru、Xie Lin、Hu Kuan、Fujinaga Masayuki、Yu Qing-zhen、Shao Tuo、Collier Thomas Lee、Josephson Lee、Shao Yi-han、Du Yun-fei、Wang Lu、Xu Hao、Zhang Ming-rong、Liang Steven H
  • Journal Title: Acta Pharmacologica Sinica Volume: 42 Pages: 491～498
  • DOI: 10.1038/s41401-020-0456-9
  • Peer Reviewed / Int'l Joint Research
• [Presentation] RADIOLABELLING AND PET IMAGING OF COPPER-64 LABELED ISODGR DERIVATIVE (2021)
  • Author(s): Masayuki Hanyu , Lin Xie , Hu Kuan , Yiding Zhang , Ming-Rong Zhang
  • Organizer: 第57回ペプチド討論会
• [Presentation] Whole-body PET Tracking of a D-dodecapeptide and its Radiotheranostic Potential for PD-L1 overexpressed tumors (2021)
  • Author(s): Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
  • Organizer: SNMMI2021
  • Int'l Joint Research
• [Presentation] PET imaging of PD-L1 overexpressing tumors with a 68Ga labeled D-dodecapeptide (2021)
  • Author(s): Hu Kuan , Xie Lin , Hanyu Masayuki , Yiding Zhang , Zhang Ming-Rong
  • Organizer: eSRS
  • Int'l Joint Research
• [Presentation] PEGylation modulation of peptides promotes PET detection of cancers (2021)
  • Author(s): Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
  • Organizer: eSRS
  • Int'l Joint Research
• [Presentation] Stapled Peptide-based radiotheranostics agent targeting MDM2 suppresses p53-mutant tumor growth (2021)
  • Author(s): Hu Kuan , Xie Lin , Yiding Zhang , Hanyu Masayuki , Zhang Ming-Rong
  • Organizer: SNMMI2021 ANNUAL MEETING
  • Int'l Joint Research
• [Presentation] Positron Emission Tomography Imaging of Vascular Endothelial Growth Factor Receptor Expression with a new 64Cu labeled peptide (2020)
  • Author(s): Hu, Kuan Shang, Jingjie Xie, Lin Hanyu, Masayuki Zhang, Yiding Yang, Zhimin Yang, Zhimin Xu, Hao Wang, Lu Zhang, Ming-Rong
  • Organizer: SNMMI 2020 Annual Meeting
  • Int'l Joint Research
• [Presentation] Development of novel 18F-labeled PET tracers for imaging TSPO with insensitivity to rs6971 polymorphism (2020)
  • Author(s): Lingling Zhang , Masayuki Fujinaga , Bin Ji , Hu Kuan , Weijian Ye , Lin Xie , Yiding Zhang , Lu Hou , Hao Xu , Ming-Rong Zhang , Wang Lu
  • Organizer: SNMMI 2020 Annual Meeting
  • Int'l Joint Research
• [Presentation] PET Imaging of VEGFR with a Novel <SUP>64</SUP>Cu Labeled Peptide (2020)
  • Author(s): Hu Kuan , Lin Xie , Yiding Zhang , Masayuki Hanyu , Ming-Rong Zhang
  • Organizer: 第60回日本核医学会学術総会
• [Presentation] Harnessing PD-L1 interface peptide for PET imaging of PD-1 immune checkpoint (2020)
  • Author(s): Hu Kuan , Lin Xie , Yiding Zhang , Masayuki Hanyu , Ming-Rong Zhang
  • Organizer: 第60回日本核医学会学術総会
• [Presentation] 癌蛋白質mGluR1に基づくがん種横断的な211At-AITM標的アイソトープ治療法の開発 (2020)
  • Author(s): 謝 琳 , 張 露露 , 破入 正行 , 藤永 雅之 , 張 一鼎 , 峯岸 克行 , Hu Kuan , 李 惠子 , 長谷川 純崇 , 永津 弘太郎 , 張 明栄
  • Organizer: 第60回日本核医学会学術総会